Ancistroheynine a, the first 7,8′-coupled naphthylisoquinoline alkaloid from Ancistrocladus heyneanus

A Photometric Screening Method for Dimeric Naphthylisoquinoline Alkaloids and Complete On-Line Structural Elucidation of a Dimer in Crude Plant Extracts, by the LC−MS/LC−NMR/LC−CD Triad

“…Even more interesting was a weak, but significant correlation observed between H-1′ and 1-CH 3 , as such long-range dipolar couplings are suitable for the determination of the axial configuration of naphthylisoquinoline alkaloids. 43,44 This is a remarkable improvement since, in earlier online investigations, ROE correlations between the biaryl parts never had been observed, [26][27][28][29] for the likewise 7,8′-coupled (albeit partially dehydrogenated) moiety of dimers such as korundamine A (2) (see Figure 1) not even off line. 5 The fact that the two "outer" biaryl axes of 4 are configurationally stable was further confirmed by HPLC-CD experiments.…”

Immunohistochemical localization of caffeine in young Camellia sinensis (L.) O. Kuntze (tea) leaves

“…The alkaloid ancistroheynine A was found in the tip of the shoot and leaf midrib of Liana Ancistrocladus heyneanus and ancistrocladine was found in the branch root of the plant by FT-Raman investigations (Urlaub et al 1997). Many more articles are published describing the localization of different alkaloids with different techniques (Verzár -Petri 1975;Yoder and Mahlberg 1976;Furr and Mahlberg 1981;Neumann et al 1983;Platt and Thomson 1992;Bringmann et al 1996;Mösli Waldhauser and Baumann 1996;Meininger et al 1997;Cai et al 1999;Corsi and Bottega 1999;Bottega et al 2004;Pasqua et al 2004;Alcantara et al 2005;Frosch et al 2006Frosch et al , 2007aNikolakaki and Christodoulakis 2006;Mesjasz -Przybyiowicz et al 2007;Liang et al 2009;Moraes et al 2009;Argyropoulou et al 2010;Christodoulakis et al 2010). …”

Ancistroheynine B and two further 7,3′-coupled naphthylisoquinoline alkaloids from Ancistrocladus heyneanus Wall.

“…itself, by the pioneering work of late Govindachari (Govindachari et al, 1970, 1972, 1973, among them ancistrocladine (1), which is 5,1 0 -coupled, ancistrocladisine (2), whose naphthalene and isoquinoline portions are coupled via C-7 and C-1 0 , and ancistrocladidine (3), which has a 7,3 0 -axis. In later investigations, we have observed the -mainly stress-induced -formation of ancistroheynine A (4), whose biaryl axis is located between C-7 and C-8 0 , from aging shoots of the plant (Bringmann et al, 1996a). Very recently, the novel isoquinolinium salt ancisheynine (5, counteranion not known) has been discovered in the aerial parts of A. heyneanus Wall.…”